Category: amides-buliding-blocks

Synthetic Route of 63920-73-0,Some common heterocyclic compound, 63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide, molecular formula is C9H12N2O3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 126 Preparation of 5,7-Dimethoxy-2-(3-methoxyphenyl)quinazolin-4(3H)-one A mixture of 2-amino-4,6-dimethoxybenzamide (0.0600 g, 0.306 mmol), 3-methoxybenzaldehyde (0.306 mmol), NaHSO3 (94%, 0.0474 g, 0.428 mmol), and p-TsOH.H2O (0.0175 g, 0.0918 mmol) in DMA (3.06 mL) was heated at 140 C. for 20 hours. The mixture was diluted with EtOAc (300 mL), washed with water (3*75 mL), then brine (75 mL), dried over sodium sulfate, filtered, and concentrated under vacuum. The residue was purified on silica gel (40 g, CH2Cl2/MeOH) and the product was freeze-dried from MeCN/H2O to provide the title compound (69%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6): delta 12.04 (s, 1H), 7.82-7.70 (m, 2H), 7.43 (t, J=7.98 Hz, 1H), 7.13 (dd, J=8.19, 2.46 Hz, 1H), 6.76 (d, J=2.19 Hz, 1H), 6.55 (d, J=2.19 Hz, 1H), 3.92-3.82 (m, 9H); MS (APCI) m/z 313 [C17H16N2O4+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-4,6-dimethoxybenzamide, its application will become more common.

Reference:
Patent; Resverlogix Corp.; Hansen, Henrik C.; (96 pag.)US9238640; (2016); B2;,
Amide – Wikipedia,
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Electric Literature of 127828-22-2,Some common heterocyclic compound, 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, molecular formula is C9H20N2O3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a solution of mono-Boc protected diamine linker (0.1 mmol, 1 eq) and iBET726(36 mg, 0.1 mmol, 1 eq) in DMF (1 mL), COMU (43 mg, 0.1 mmol, 1 eq) and DIPEA (48 mircoL) were added. The reaction mixture was stirred at room temperature for 1 hour, then quenched with ice cold water. Volatiles were removed in vacuum and the crude mixture was purified by preparative HPLC (METHOD 2). Fractions containing the desired product were evaporated under reduced pressure and the reside was dissolved in DCM (1 mL) and treated with a solution of anhydrous HC1 in dioxane (4M, 1 mL). After 1 hour, volatiles were removed under reduced pressure and the reside was freeze dried in order to remove any excess of acid. Analytical data (HRMS) are provided in table III shown below.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, its application will become more common.

Reference:
Patent; UNIVERSITY OF DUNDEE; TESTA, Andrea; HUGHES, Scott; BUTCHER, Steven Peter; CIULLI, Alessio; (279 pag.)WO2019/238886; (2019); A1;,
Amide – Wikipedia,
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Application of 116195-15-4,Some common heterocyclic compound, 116195-15-4, name is (R)-(-)-(2-Methylacryloyl)-2,10-camphorsultam, molecular formula is C14H21NO3S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step 2. Synthesis of (3aS,6R,7aR)-8,8-dimethyl-1-{[(5R)-5-methyl-4,5-dihydro-1 H-pyrazol-5- yl]carbonyl}hexahydro-3a,6-methano-2, 1 -benzisothiazole 2,2-dioxideTMSCHN262% Procedure: To a solution of (trimethylsilyl)diazomethane in ether (2M; 20ml) was added the solid (3aS,6R,7aR)-1 -methacryloyl-delta.delta-dimethylhexahydro-Sa.beta-methano^.i -benzisothiazole 2,2-dioxide and then the reaction mixture was stirred at room temperature for 72 hours. A solution formed. The solution was evaporated in vacuo and then diluted with methylene chloride (50ml), cooled to 0 C and then trifluoroacetic acid (1.2ml) was added drop wise. The mixture was stirred for 2h at 00C. The reaction mixture was diluted with ethyl acetate (200ml) and washed with sat. NaHCO3 (200 imL). The organic phase was washed with brine (200 mL) and then dried with magnesium sulfate. The organic solvents were removed in vacuo and the product purified by silica gel chromatography (eluant 10-100 EtOAc in hexane) and then treated with ether. The product was isolated as a solid (2.9Og, 56% yield). Optical rotation = 0.02Og in 2ml; c=0.01g/ml {C= 1 (CHCI3)); measurement -0.287; optical rotation = – 0.287×4000/10 = – 114.8 (using a Perkin-Elmer 241 Polarimeter).Combustion Analysis:1 H NMR (400 MHz, DMSO-D6) delta ppm 0.87 (m, 3 H), 0.98 (s, 3 H),1.21 (m, 1 H), 1.32 (s, 3 H), 1.40 (m, 1 H), 1.71 (m, 4 H), 1.85 (dd, J=13.35, 7.70 Hz, 1 H), 2.54 (dd, J=17.16, 1.56 Hz, 1 H), 3.13 (dt, J=17.20, 1.34 Hz, 1 H)1 3.64 (d, J=14.04 Hz, 1 H), 3.74 (d, J=14.04 Hz1 1 H), 3.83 (dd, J=7.60, 4.68 Hz, 1 H), 6.62 ;(t, J=1.46 Hz, 1 H), 6.78 (S1 1 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (R)-(-)-(2-Methylacryloyl)-2,10-camphorsultam, its application will become more common.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/65503; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 683-57-8, name is 2-Bromoacetamide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Bromoacetamide

Example 304J 2-({3-[1-(cyclobutylamino)-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl]-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl}oxy)acetamide The product of Example 3041 (0.048 g, 0.11 mmol) in N,N-dimethylformamide (2 ML) was reacted with cesium carbonate (0.15 g, 0.45 mmol), bromoacetamide (0.026 ML, 0.18 mmol), and a catalytic amount of tetrabutylammonium iodide at 25 C. for 3 hours.The reaction was concentrated under a stream of nitrogen stream of nitrogen warmed through a manifold heated to 165 C. and the resulting residue was triturated with water, filtered and dried.The resulting solid was triturated in hot ethyl acetate, filtered, and dried to give the title compound (0.020 g, 37%). MS (ESI-) m/z 482 (M-H)-. 1H NMR (300 MHz, DMSO-d6) delta ppm 1.59 (m, 2H) 1.99 (m, 4H) 3.60 (m, 1H) 4.49 (s, 2H) 6.08 (d, J=6.62 Hz, 1H) 7.05 (t, J=7.17 Hz, 1H) 7.20 (m, 3H) 7.40 (s, 1H) 7.50 (m, 1H) 7.65 (m, 2H) 8.05 (d, J=7.72 Hz, 1H) 16.25 (s, 1H).The sodium salt of the title compound was prepared according to the procedure of Example 1D. 1H NMR (300 MHz, DMSO-d6) delta ppm 1.59 (m, 1H) 1.99 (m, 4H) 3.61 (m, 2H) 4.49 (s, 2H) 6.08 (d, J=6.62 Hz, 1H) 7.05 (m, 1H) 7.21 (m, 2H) 7.40 (s, 2H) 7.50 (m, 1H) 7.64 (m, 2H) 8.06 (dd, J=7.91, 1.29 Hz, 1H) 8.32 (s, 1H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 683-57-8.

Reference:
Patent; Pratt, John K.; Betebenner, David A.; Donner, Pamela L.; Green, Brian E.; Kempf, Dale J.; McDaniel, Keith F.; Maring, Clarence J.; Stoll, Vincent S.; Zhang, Rong; US2004/167123; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 40724-47-8, name is 4-Bromomethylbenzenesulfonamide, A new synthetic method of this compound is introduced below., Quality Control of 4-Bromomethylbenzenesulfonamide

To a stirring solution of 4-(4-(difluoromethoxy)-2-hydroxy-3-methoxyphenyl)-2,3- dihydro-lH-inden-l-one (80 mg, 0.25 mmol) in acetonitrile (10 ml_), was added potassium carbonate (104 mg, 0.75 mmol) and 4-bromomethyl-benzenesulfonamide (125 mg, 0.5 mmol) and the resultant reaction mixture was heated to 80 ¡ãC for 16 h. The reaction mixture was cooled to RT and filtered through celite and the filtrate was concentrated under reduced pressure. The residue was purified by columnchromatography (silica gel, 0-70percent ethyl acetate in pet ether) to afford title compound as a solid (40 mg, 33percent).UPLC-MS (M + l) : 490.11 ; UPLC-MS RT (min) : 2.4

The synthetic route of 40724-47-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEO PHARMA A/S; NIELSEN, Simon Feldbaek; HORNEMAN, Anne Marie; LAU, Jesper Faergemann; LARSEN, Jens Christian H¡ãjland; WO2011/134468; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 563-83-7, name is Isobutyramide, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: Isobutyramide

General procedure: To a mixture of amide (2 mmol) and amine (2.6 mmol) ina 10 mL round bottomed ask was added [PyPS]3PW12O40 (140 mg, 0.04 mmol). The reaction mixture was stirred at the corresponding temperature under MW (700 W). The progress of the reaction was monitored by TLC. On completion, the mixture was diluted with ethyl acetate (20 mL) with stirring for 30 min. The insoluble catalyst was recovered by filtration or centrifugation. The filtrate was evaporated and the residue in almost pure form. Recrystallization or column chromatography could be used for further purication.

The synthetic route of Isobutyramide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fu, Renzhong; Yang, Yang; Chen, Zhikai; Lai, Wenchen; Ma, Yongfeng; Wang, Quan; Yuan, Rongxin; Tetrahedron; vol. 70; 50; (2014); p. 9492 – 9499;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 35303-76-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 35303-76-5 name is 4-(2-Aminoethyl)benzenesulfonamide, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A solution of 3- (4-fluorophenyl) propan-l-amine hydrochloride(2.11 mmol) in THF (10 ml)Was added DIPEA (6.32 mmol) and triphosgene (0.843 mmol)And the reaction mixture was stirred at 0 ¡ã C for 30 minutes.Then, 4- (2-aminoethyl) benzenesulfonamide (2.11 mmol) was added thereto,The reaction mixture was warmed to room temperature and stirred for 16 hours.To the reaction mixture was added 10percent [v / v] sodium hydrogencarbonate solution (20 ml) and extracted with ethyl acetate (3×50 ml). The ethyl acetate layer was collected and dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude extract thus obtained was purified by silica gel flash column chromatography (eluting with hexane solution containing 50 to 80percent [v / v] ethyl acetate) to give 4- – (3- (3- (4-fluorophenyl) propyl) ureido) ethyl) benzenesulfonamide was obtained

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(2-Aminoethyl)benzenesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; The Industry & Academic Cooperation in Chungnam National University (IAC); Jung, Sang-Hun; Woo, Sun-Hee; Kim, Sang- Kyum; Jeon, Eun-Seok; Lee, Yu-Jung; Meunikam, Manoj; Jalani, Hiteshkumar; Sharma, Niti; (205 pag.)KR2016/108281; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 194920-62-2, name is tert-Butyl (3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of tert-Butyl (3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)carbamate

To a solution of t-butyl N-(13-amino-4,7,10-trioxatridecyl) carbamate (85.1 mg, 0.266 mmol),7-(diethylamino)coumarin-3-carboxylic acid hydrochloride (70.0 mg, 0.235 mmol), and 4-methylmorpholine (26.0 muL,0.235 mmol) in MeOH (1 mL) was added DMT-MM (77.5 mg,0.280 mmol) at rt. After being stirred for 3 h at rt, the solvent was removed under vacuum. The residue was loaded on asilica gel column and eluted with CHCl3/MeOH (97 : 3) to give a crude product (173.5 mg, inseparable amine adduct of dimethoxytriazine was contained), which was dissolved in dioxane (0.5 mL), and then treated with conc. HCl (0.5 mL) at rt for 3 h. The solvent of the resulting mixture was removed under vacuum. The crude compound was purified by decantation with MeOH (containing 0.5 M HCl)-Et2O at rt to give the desired compound as a yellow solid (105.1 mg, 83% over 2steps). mp: 251-252C. 1H-NMR (methanol-d4) delta: 1.23 (6H, t,J=7.0 Hz), 1.82-1.97 (4H, m), 3.12 (2H, t, J=6.4 Hz), 3.46-3.74(18H, m), 6.58 (1H, d, J=2.5 Hz), 6.83 (1H, dd, J=2.5, 9.2 Hz),7.56 (1H, d, J=9.2 Hz), 8.63 (1H, s). 13C-NMR (methanol-d4)delta: 12.7, 28.0, 30.4, 38.3, 40.3, 46.0, 70.1, 70.5, 71.0, 71.1, 71.2,71.4, 97.3, 109.5, 110.1, 111.7, 132.7, 149.3, 151.6, 159.2, 164.0,165.4. IR (CHCl3) cm-1: 3007, 1697, 1616, 1540, 1511, 1134.FAB-MS m/z: 464.2755 (Calcd for C24H38N3O6: 464.2761). MS(ESI) m/z: 464 (M-72)+.

The synthetic route of 194920-62-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kunishima, Munetaka; Kato, Daiki; Nakanishi, Shuichi; Kitamura, Masanori; Yamada, Kohei; Terao, Keiji; Asano, Tomoya; Chemical and Pharmaceutical Bulletin; vol. 62; 11; (2014); p. 1146 – 1150;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6083-47-2, name is 4-(Dimethylamino)benzamide, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 6083-47-2, 6083-47-2

General procedure: A 12 mL vial was charged with Pd(OAc)2 (2 mol%), BuPAd2 (6 mol%), and a stirring bar. Then, 2 ml dioxane and 1 mmol of bromobenzene were injected by syringe. The vial (or several vials) was placed in an alloy plate, which was transferred into a 300 mL autoclave of the 4560 series from Parr Instruments under argon atmosphere. After flushing the autoclave three times with NH3, a pressure of 2 bar NH3 and 2 bar CO was adjusted at ambient temperature. Then, the reaction was performed for 16 hours at 100 oC. After the reaction is finished, the autoclave was cooled down to room temperature and the pressure was released carefully. Then, CuI (5 mol%), DMEDA (10%), K2CO3 (3 mmol) and 1,2-dibromobenzene were added in under air, the vial was closed and heated to 110oC for 20 hours. The reaction mixture cooled down to room temperature. The solution was extracted 3-5 times with 2-3 ml of ethyl acetate from aqua solution. After evaporation of the organic solvent the residue was adsorbed on silica gel and the crude product was purified by column chromatography using n-heptane/AcOEt (20:1) as eluent.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-(Dimethylamino)benzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wu, Xiao-Feng; Neumann, Helfried; Neumann, Stephan; Beller, Matthias; Tetrahedron Letters; vol. 54; 24; (2013); p. 3040 – 3042;,
Amide – Wikipedia,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, This compound has unique chemical properties. The synthetic route is as follows., 121492-06-6

General procedure: 5-Amino-(30-[N0-methyl-N0-tert-butoxycarbonyl]propyl)-3-(N,N-dimethylcarbox-amide)-6-nitrochromane (9a).[29]A mixture of 5-chloro-3-N,N-dimethyl-carboxamide-6-nitro-chromane (8) (300 mg, 1.10 mmol), primary amine N-Boc-N-methyl-1,3-trimethylenediamine (18) (5.50 mmol),and N-methyl-pyrrolidinone (1.0 mL) was heated in a sealedtube at 758C for 48 h. The reaction mixture was poured into amixture of diethyl ether and water (1 : 1, 80 mL) and the mixturestirred for 30 min. The mixture was transferred to a separationfunnel and the ether layer washed with water (4 25 mL). Theorganic phase was dried over anhydrous sodium sulfate, filtered,and evaporated under reduced pressure. The crude product waspurified by flash chromatography (silica gel, 5 % methanol indichloromethane). The product 9a[29]was isolated as a brightyellow oil (381 mg, 87 %).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Schmit, David; Milewicz, Urszula; Boerneke, Mark A.; Burley, Scott; Walsworth, Kevin; Um, Joann; Hecht, David; Hermann, Thomas; Bergdahl, B. Mikael; Australian Journal of Chemistry; (2020);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics